#------------------------------------------------------------------------------
#$Date: 2015-12-30 12:21:14 +0200 (Wed, 30 Dec 2015) $
#$Revision: 171761 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/06/2240634.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2240634
loop_
_publ_author_name
'Heckel, Ricarda'
'Hulliger, Jürg'
'Schwarzer, Anke'
'Weber, Edwin'
_publ_section_title
;
 Crystal structure of 4'-bromo-2,3,5,6-tetrafluorobiphenyl-4-carbonitrile
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o347
_journal_page_last               o348
_journal_paper_doi               10.1107/S2056989015007847
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C13 H4 Br F4 N'
_chemical_formula_moiety         'C13 H4 Br F4 N'
_chemical_formula_sum            'C13 H4 Br F4 N'
_chemical_formula_weight         330.08
_chemical_name_systematic
;
4'-Bromo-2,3,5,6-tetrafluorobiphenyl-4-carbonitrile
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3560(15)
_cell_length_b                   12.107(2)
_cell_length_c                   12.723(3)
_cell_measurement_reflns_used    4750
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      28.42
_cell_measurement_theta_min      3.21
_cell_volume                     1133.1(4)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
SMART (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
XP (Sheldrick, 2008)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), publCIF (Westrip, 2010)
and SHELXLE
(Hübschle et al.,  2011)
;
_computing_structure_refinement
;
SHELXL2012 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXTL (Sheldrick, 2008)
;
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18347
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.801
_diffrn_reflns_theta_min         2.322
_exptl_absorpt_coefficient_mu    3.663
_exptl_absorpt_correction_T_max  0.718
_exptl_absorpt_correction_T_min  0.486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_description       splitter
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.493
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.097
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.311
_refine_ls_abs_structure_details
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.011(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0277
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[σ²(Fo²)+(0.0144P)²]
where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0505
_refine_ls_wR_factor_ref         0.0521
_reflns_number_gt                2930
_reflns_number_total             3234
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2464sup1.cif
_cod_data_source_block           I
_cod_database_code               2240634
_cod_database_fobs_code          2240634
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.265
_shelx_estimated_absorpt_t_max   0.718
_shelxl_version_number           .000002012
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Br Br1 0.89811(4) 0.35795(3) 0.37922(2) 0.01853(8) Uani d 1
F F1 0.7744(2) 1.00596(16) 0.75920(12) 0.0196(4) Uani d 1
F F2 0.7639(2) 0.79698(15) 0.69387(12) 0.0179(4) Uani d 1
F F3 1.0359(2) 0.90632(14) 0.37137(13) 0.0163(4) Uani d 1
F F4 1.0323(2) 1.11450(14) 0.43493(13) 0.0196(4) Uani d 1
N N1 0.9005(4) 1.2681(2) 0.66563(19) 0.0208(6) Uani d 1
C C1 0.9026(4) 1.1790(2) 0.6343(2) 0.0161(6) Uani d 1
C C2 0.9029(5) 1.0664(2) 0.5984(2) 0.0153(6) Uani d 1
C C3 0.8371(4) 0.9812(3) 0.6627(2) 0.0154(7) Uani d 1
C C4 0.8354(4) 0.8729(3) 0.6295(2) 0.0147(6) Uani d 1
C C5 0.9004(4) 0.8418(2) 0.5296(2) 0.0131(6) Uani d 1
C C6 0.9650(4) 0.9283(3) 0.4667(2) 0.0129(6) Uani d 1
C C7 0.9665(4) 1.0369(3) 0.4992(2) 0.0144(6) Uani d 1
C C8 0.8998(5) 0.7249(2) 0.4938(2) 0.0133(6) Uani d 1
C C9 0.9476(4) 0.6389(3) 0.5620(2) 0.0145(6) Uani d 1
H H9 0.9807 0.6555 0.6324 0.017 Uiso calc 1
C C10 0.9474(4) 0.5302(3) 0.5286(2) 0.0161(7) Uani d 1
H H10 0.9795 0.4725 0.5756 0.019 Uiso calc 1
C C11 0.8997(5) 0.5065(2) 0.4254(2) 0.0148(6) Uani d 1
C C12 0.8517(4) 0.5894(3) 0.3554(2) 0.0153(7) Uani d 1
H H12 0.8191 0.5720 0.2851 0.018 Uiso calc 1
C C13 0.8520(4) 0.6986(3) 0.3898(2) 0.0142(6) Uani d 1
H H13 0.8196 0.7560 0.3424 0.017 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 C2 178.1(3)
C7 C2 C3 117.1(3)
C7 C2 C1 122.1(3)
C3 C2 C1 120.8(2)
F1 C3 C4 119.3(3)
F1 C3 C2 119.1(3)
C4 C3 C2 121.6(3)
F2 C4 C3 118.0(3)
F2 C4 C5 120.1(3)
C3 C4 C5 121.9(3)
C6 C5 C4 115.5(3)
C6 C5 C8 122.5(2)
C4 C5 C8 122.0(3)
F3 C6 C7 117.1(3)
F3 C6 C5 119.8(3)
C7 C6 C5 123.0(3)
F4 C7 C6 119.3(3)
F4 C7 C2 119.8(3)
C6 C7 C2 120.9(3)
C9 C8 C13 118.6(3)
C9 C8 C5 121.2(2)
C13 C8 C5 120.3(3)
C10 C9 C8 121.1(3)
C10 C9 H9 119.4
C8 C9 H9 119.4
C9 C10 C11 119.2(3)
C9 C10 H10 120.4
C11 C10 H10 120.4
C12 C11 C10 121.4(3)
C12 C11 Br1 119.1(2)
C10 C11 Br1 119.5(2)
C11 C12 C13 119.0(3)
C11 C12 H12 120.5
C13 C12 H12 120.5
C12 C13 C8 120.7(3)
C12 C13 H13 119.6
C8 C13 H13 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C11 1.892(3)
F1 C3 1.346(3)
F2 C4 1.339(3)
F3 C6 1.347(3)
F4 C7 1.336(3)
N1 C1 1.150(4)
C1 C2 1.438(4)
C2 C7 1.393(4)
C2 C3 1.402(4)
C3 C4 1.377(4)
C4 C5 1.409(4)
C5 C6 1.401(4)
C5 C8 1.487(4)
C6 C7 1.379(4)
C8 C9 1.400(4)
C8 C13 1.406(4)
C9 C10 1.383(4)
C9 H9 0.9500
C10 C11 1.389(4)
C10 H10 0.9500
C11 C12 1.388(4)
C12 C13 1.392(4)
C12 H12 0.9500
C13 H13 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C9 H9 F2 0.95 2.47 2.882(4) 106.3
C13 H13 F3 0.95 2.45 2.865(3) 106.6
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C7 C2 C3 F1 179.9(3)
C1 C2 C3 F1 -0.5(4)
C7 C2 C3 C4 0.1(5)
C1 C2 C3 C4 179.7(3)
F1 C3 C4 F2 2.6(4)
C2 C3 C4 F2 -177.5(3)
F1 C3 C4 C5 -179.5(3)
C2 C3 C4 C5 0.3(5)
F2 C4 C5 C6 177.3(3)
C3 C4 C5 C6 -0.5(4)
F2 C4 C5 C8 -2.6(4)
C3 C4 C5 C8 179.6(3)
C4 C5 C6 F3 177.6(2)
C8 C5 C6 F3 -2.4(4)
C4 C5 C6 C7 0.2(4)
C8 C5 C6 C7 -179.8(3)
F3 C6 C7 F4 1.8(4)
C5 C6 C7 F4 179.3(3)
F3 C6 C7 C2 -177.3(3)
C5 C6 C7 C2 0.2(5)
C3 C2 C7 F4 -179.4(3)
C1 C2 C7 F4 1.0(5)
C3 C2 C7 C6 -0.3(4)
C1 C2 C7 C6 -179.9(3)
C6 C5 C8 C9 139.2(3)
C4 C5 C8 C9 -40.8(4)
C6 C5 C8 C13 -40.4(5)
C4 C5 C8 C13 139.6(3)
C13 C8 C9 C10 -0.3(4)
C5 C8 C9 C10 -179.9(3)
C8 C9 C10 C11 0.3(4)
C9 C10 C11 C12 -0.2(5)
C9 C10 C11 Br1 -179.8(2)
C10 C11 C12 C13 0.1(5)
Br1 C11 C12 C13 179.7(2)
C11 C12 C13 C8 -0.1(4)
C9 C8 C13 C12 0.2(4)
C5 C8 C13 C12 179.8(3)
